Potassium Hydroxide → 3-(Trifluoromethyl)pyrazine-2-carboxylic acid

HRID 604824Notes

Reaction equation

HRID 604824 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[C:4]([C:9]([O:11]C)=[O:10])=[N:5][CH:6]=[CH:7][N:8]=1.[OH-].[K+]>C(O)C.O>[F:14][C:2]([F:1])([F:13])[C:3]1[C:4]([C:9]([OH:11])=[O:10])=[N:5][CH:6]=[CH:7][N:8]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 58542464Methyl 3-(trifluoromethyl)pyrazine-2-carboxylate

Product 1

HCID 536308603-(Trifluoromethyl)pyrazine-2-carboxylic acidYield 63%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

Methyl 3-trifluoromethylpyrazine-2-carboxylate (700 mg, 3.4 mmol) was dissolved in ethanol-water (1:1, 10 ml), followed by adding potassium hydroxide (300 mg) and refluxing under heating for 1 hour. The reaction solution was concentrated under reduced pressure, followed by dilution of residue with water and washing with ethyl acetate. The water layer was acidified with HCl, followed by extracting with ethyl acetate, washing with a saturated brine. The solution was dried over magnesium sulfate, and concentrated under reduced pressure to obtain 409 mg of the desired compound as crystal.

Workup

  1. temperaturerefluxing
  2. temperatureunder heating for 1 hour
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. washwashing with ethyl acetate
  5. extractionby extracting with ethyl acetate
  6. washwashing with a saturated brine
  7. dry with materialThe solution was dried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1ba288a353424b96977a68062f07fada
Source dataset
uspto-grants-2011_03
Patent number
US07910735B2

Reaction notes

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